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Stewart once lived in South Side, Chicago. In 1914, one of Stewart's trysts summoned Anyanka, who then cursed Stewart by turning him into a demon for his blatant philandering. To make things even worse for Stewart, Anyanka sent him to a Hell dimension where he was tortured for some time.

Over the course of the next eight decades, Stewart spent his time planning his revenge. He finally returned to Earth, arriving in Sunnydale, just as Anyanka was marrying Xander Harris.

Appearing as an elderly human man, Stewart introduced himself as Xander's future self, subsequently showing Xander visions of the worst possible futures he and Anya could share through a Sphere of the Future, claiming that they would actually happen.

This served as a catalyst to Xander's already waning thoughts on marriage, and he left Anya standing at the alter soon after. Anya then confronted Stewart, who, satisfied, revealed himself to her. After a brief scuffle with Buffy Summers, Xander returned and finished Stewart off with a large pillar, although he still backed out of the wedding out of fear of the possibility of the future Stewart presented.